Not all consultants are worth it. Some drive real impact. Others just burn your time and budget.

In this episode, Toni and Raul dive into how to tell the difference. They break down when it actually makes sense to bring in outside help, how to vet someone properly, and the biggest red flags to avoid.

You'll learn why consulting is a real skill, what good execution support looks like, and how to think about pricing and value.

• (00:00) - Introduction
• (02:48) - Do you actually need consultants?
• (05:22) - The consulting relationship with startups
• (08:29) - Identifying red flags
• (10:41) - The hammer people
• (16:17) - Consulting is a skill
• (21:14) - Consultants as challengers
• (24:40) - Pricing and value in consulting
• (30:06) - Execution and enablement
• (33:38) - Summary
• (35:45) - Next week: Chris Tottman on VCs

In a world of AI-generated noise and automated outreach, Cliff Simon has built a multi-million dollar business by doing something simple but rare: showing up in person.

In this episode, Cliff shares how he turned events, community dinners, and authentic relationships into a powerful go-to-market strategy. He breaks down why most event-based approaches fail, what it really means to play the long game, and how founders and revenue leaders can drive growth without relying on cold outreach.

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• (00:00) - Introduction
• (01:53) - The Importance of In-Person
• (06:01) - The Role of Pavilion
• (08:08) - Building Relationships
• (12:09) - Building for Long Term
• (16:41) - Modern Networking Tactics
• (21:58) - Evaluating Event Success
• (24:57) - Common Misconceptions in Event Strategy
• (26:34) - Effective Event Strategies
• (31:39) - The Power of Personal Branding
• (32:13) - Comparing Rev Ops Events
• (36:28) - Next Week: What You Need to Know About Consultants

We sat down and unpacked the messy, unfiltered reality of being a startup CEO.

The kind no one tells you about. Not at panels. Not in TechCrunch puff pieces. And definitely not on LinkedIn.

This isn’t a “how I built this” highlight reel. It’s what actually happens when you’re juggling investors, layoffs, spin cycles, fundraising failures, and the kind of decisions that keep you up for months.

We dig into why CEO life is less “Davos and private jets” and more “burnout, pressure, and zero control.” What it’s like to be the person everyone expects answers from, even when you’re not sure yourself. And why founders need less hype—and way more empathy.

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• (00:00) - Introduction
• (01:44) - Inside the minds of CEOs
• (06:47) - Transparency and communication
• (08:37) - Dealing with the worst problems
• (09:51) - Limited control and influence
• (10:59) - Fundraising challenges
• (15:54) - Financial realities of CEOs
• (24:57) - The emotional toll
• (27:24) - Decision-making pressures
• (37:16) - Final thoughts